This ancient port in Sicily's deep south has always been a little rough around the edges—the perfect combination of refined and unmistakably real.

ByLee Marshall on March 30, 2010

The man to know in Syracuse is Pietro Beneventano del Bosco, a dashing Sicilian baron with a schoolboy glint in his eyes who's one part Il Gattopardo and one part Benny Hill. His family home, Palazzo Beneventano del Bosco, is among the most beautiful of Sicily's Baroque townhouses, all frescoes and manorial charm. But maintaining a damned fine crash pad is only one of il barone's talents. Another is his feel for the history, traditions, and mind-set of his hometown, which makes Del Bosco an authority on everything from Moscato di Siracusa dessert wine (he produces barrels of it on his country estate) to the impenetrable dialect of the local fishermen.

The baron's family arrived in Sicily in the 14th century, so it's hardly surprising that he takes the long view of history. As we chug and dawdle around the harbor in his private gozzo—a prewar fishing vessel, a rarity in Sicily nowadays—Del Bosco points out a small islet in the bay, a tilted rocky platform that just breaks the surface. "That," he tells me, "is where the Athenians set up a trophy when they sank eleven Syracusan ships." It's as if he is filling me in on last week's soccer scores or last month's mayoral election, rather than sharing an obscure detail of a siege that took place in 413 B.C.

In Sicily's deep south, past and present are like blood cousins who spend a lot of time in each other's company. Recently Syracuse's rough, ancient magic and its untidy mix of old and new (soccer shirts hang-dry from glorious Rococo balconies) have attracted increasing numbers of tuned-in independent travelers. It's not that Syracuse is becoming the new Taormina (located 75 miles north). It's that visitors are increasingly looking for an anti-Taormina, a Sicilian town steeped in history but nonetheless possessed of an authentic edge. True, Taormina has nice hotels and its residents are used to dealing with crazy foreigners and their crazy needs. But mass tourism has turned the eastern hill town into a souvenir-clogged day-trip resort, obscuring what's special about the region: ancient Greek theaters and elemental views of sky and sea. Syracuse, on the other hand, is refined but unmistakably real, the antidote to the Taormina experience.

But first let's step back and get our bearings. Draw a line from Catania on Sicily's east coast across to Gela on the southern seaboard, and detach, in your mind, the irregular triangle below the line. On the eastern side of this mammarian appendage is Syracuse, perched on a promontory dominating the island's largest natural harbor. South of here, past the Baroque town of Noto, the coast ends at the wild tip of Capo Passero, home to windsurfers, migrating birds, and an abandoned tuna fishery. Inland, to the west, are the towns of Modica and Ragusa, unjustly neglected by all but the most adventurous of European and American tourists; Ragusa Ibla, the honey-colored Old Town, is one of Sicily's ten great sites.

Ortygia, however, is up there in the top three. The original nucleus of the city of Syracuse, Ortygia began life as an island connected to the mainland by a thin causeway of sand, but soon became more of a peninsula, a stone raft tethered by bridges. It was here that Greek settlers first dropped anchor in the eighth century B.C., attracted by the harbor and the easy defendability of what was to become their island-fortress. The gamble paid off: Syracuse developed into the New York of Sicily, challenging the Greek homeland's economic and military prowess. Here, too, there was a war of independence, which ultimately (after the brief setback for Syracuse mentioned earlier by Del Bosco) ended with the humiliation of the Athenian fleet sent from the mother country to teach the upstart colonials a lesson.

There are no hard feelings, though. Syracuse is as proud of its Greek origins as it is of its creation myth, which involves a nymph named Arethusa who, pursued by a sex-crazed river god, swam across the sea from Greece. Just as the god was about to have his evil way, Arethusa landed on Ortygia, where she turned into a freshwater spring. To this day she can still be seen, trickling into a simple 19th-century basin that is home to frondy papyrus plants and a preening clan of ducks. The Fonte Aretusa is a symbol of Syracuse's strong links to the past and to other Mediterranean cultures. This is evident in the city's long-standing tradition of mounting Greek tragedies in the Teatro Greco, as well as in the local fishermen's habit of painting the all-seeing eye of Horus on the prow of their boats.

Between the sixth and third centuries B.C., the Greeks expanded into the mainland quarters of Achradina, Tyche, and Neapolis; today's population of 125,000 is half of that of ancient Syracuse. The landward part of the city is home to the Teatro Greco, Syracuse's biggest tourist attraction. But the archaeological area, though compelling, is surrounded by the sprawl of the modern city. Today it is Ortygia that is generating buzz. A new energy pulses from behind the peeling paint and eroded sandstone facades of this fascinating historical layer cake. This renaissance dates back to 1989, when a plan was launched to reverse the centro storico's slow decline with an influx of EU and governmental funds. Now the medieval palazzi are emerging from under wraps, and the Castello Maniace, the great military bulwark on the peninsula's tip, is nearing the end of a major renovation that will bring to light one of the symbolic military conundrums of Emperor Frederick II in all its enigmatic splendor.

During Italy's postwar economic boom, when old meant bad, young siracusani in search of action tended to avoid the Old Town. Now that old is good once more, they're back in force. Ortygia has even managed to conjure up a new ancient monument: the oldest mikvah, or Jewish ritual bath, ever found in Europe. Dating from the sixth century A.D., it was discovered in the cellar of a medieval townhouse four years ago and bears witness to the Sicilian city's strong trading and cultural links to the Levant.

Barone Beneventano del Bosco has also done his bit for the tourist cause: He set aside a suite of rooms in Palazzo Beneventano for the grandest of modern-day Grand Tourists. He is motivated to do this not so much by the desire to earn a few euros but by the same disinterested instinct that prompted his ancestors to play host to painters, literary travelers, and (on one occasion) Lord Nelson and Emma Hamilton. Old-fashioned hospitality is alive and well in Syracuse.

Places to Stay

One of Syracuse's best-known accommodations is the recently refurbished Hotel des Etrangers et Miramare, but the service can be abrupt and the boxy, business-oriented layout of the rooms is uninspiring. Head instead for the simple and unpretentious Hotel Gutkowski (rate, $110; 26 Lungomare Vittorini; 39-0931/465-861; www.guthotel.it), a 15-room pastel-blue charmer on Ortygia's eastern-seafront promenade. The facilities are basic but delightfully seaside-chic, and the hotel serves one of the best breakfasts in town. Dedicated Grand Tourists, however, will settle for nothing less than the suite of guest rooms at Barone Pietro Beneventano's townhouse, Palazzo Beneventano ($ rate, $5,000 for a minimum three-night stay; reservations through London-based rental agency Lanza & Baucina; 44-207/738-2222). The hunting-trophy room, with its unique Bugatti furniture, sets just the right tone.

Dining Out

In wave-lashed Syracuse, seafood features prominently on most menus; swordfish is especially popular, as are sea urchins, which are generally eaten raw as an antipasto. But there's also plenty of hearty peasant fare, such as lamb, rabbit, snails, and tangy sheep's cheese. Sample both at Da Mariano (dinner, $35; 9 Vicolo Zuccalà; 39-0931/67444), a humble trattoria that mixes standards like pasta con le sarde (pasta with sardines) with mountain dishes such as ricotta-filled ravioli in pork sauce. Just around the corner, La Foglia (dinner, $100; 29 Via Capodieci; 39-0931/66233; www.lafoglia.it) is a must, if only for the decor: an artful jumble of antiques, mismatched glasses and cutlery, beams painted with naïf motifs, and a menu embroidered with so much cut paper and feathers that it looks like a table setting. Patron Beppe Pravato offers a filling soup-heavy, veggie-oriented menu. We had the best meal of our stay at L'Ancora (dinner, $75; 7 Via Perno; 39-0931/462-369), which began with a delicious antipasto of raw prawns marinated in oil and lemon, with rough-chopped orange, parsley, and chiles.

Local Wines

Sicily used to be associated with the sort of crude sugar- and alcohol-rich plonk that's often used to beef up more anemic northern wines. But the last decade or so has seen a major makeover, thanks to dynamic young producers like Planeta (39-091/327-965; www.planeta.it), which now maintains four separate estates on the island. From 30 green acres south of Noto, not far from Sicily's southernmost point, Planeta coaxes two spectacular wines. Santa Cecilia is a 100 percent Nero d'Avola, a fruit-packed grape fast becoming Sicily's answer to Sangiovese. But it is the amber-hued dessert wine, produced for the first time in 2004, that blew us away—a Moscato di Noto that tastes like sultanas squeezed into a glass.

Five Sights Not to Miss

While Syracuse's fifth-century B.C. Greek theater in the Parco Archeologico (Largo Anfiteatro; 39-0931/66206; open daily at 9 a.m. until two hours before sunset) lacks Taormina's dramatic setting, it is still an atmospheric sight—especially when being used to stage Greek tragedies, which are presented at sunset in May and June.

In the seventh century A.D., when citizens began to yearn for a church worthy of Syracuse's status as Sicily's center of Christianity, the simplest solution was to brick up the spaces between the columns of the Temple of Athena, once the grandest and most opulent Greek temple outside of Greece itself. Despite later renovations, the Duomo (Piazza del Duomo; open 8 a.m.-noon and 4 p.m.-7 p.m., daily) is still recognizable as a pagan temple dressed up in Christian clothes.

A sixth-century Jewish ritual bath, or mikvah (52 Via Alagona; 39-0931/22255; open 9 a.m.-12:30 p.m., Monday-Saturday), was discovered just four years ago in the cellar of a medieval townhouse. It's a significant addition to Syracuse's already considerable selection of historic sites.

An exceptionally beautiful coastal park south of Syracuse, Vendicari Nature Reserve (six miles south of Noto; 39-0931/462-452) includes more than five miles of dunes, beaches, and brackish lagoons—perfect for birdwatchers and beachcombers.

Garden to Visit

When Princess Miki Borghese moved into the family estate near Lentini, north of Syracuse, in the sixties, the grounds around the main house were a barren expanse of mud—the sad remains of a lake that was drained in the thirties. But over the years, la principessa has transformed Le Case del Biviere ($ open April to October; for reservations, call Lanza & Baucina, 44-0207/738-2222) into one of Sicily's most delightful gardens, in which old roses creep across ancient walls and palms and jacaranda cast pools of shade on the lawn. Visits to the garden can also include lunch or afternoon tea.

Insider's Recommendations

The guide to get is Eva Greco, a personable, well-informed siracusana who is remarkably passionate about her hometown (from $135 for a half day; 39-338/755-8537).

In Europe, the only place where papyrus grows naturally is on the banks of the Ciane river, south of Syracuse. Paper made from the plant is the region's hot souvenir, but much of the stuff sold in Ortygia as genuine papyrus is of dubious origin. Not so at Galleria Bellomo (15 Via Capodieci; 39-0931/61340; www.bellomogallery.com). Flavia Massara Marotta is the leading local authority on the aquatic plant, and most days she can be seen in her shop, transforming strips of papyrus into attractive sheets of the world's oldest paper product.

Noto is the most harmonious and centrally planned of the Baroque new towns that sprang up around Syracuse in the wake of the devastating 1693 earthquake. It also has one of Sicily's best bar-pasticcerias: Caffè Sicilia (125 Corso Vittorio Emanuele; 39-0931/835-013) may not look like much on the inside, but people travel for miles for one forkful of its cassata (a ricotta-filled cake topped with marzipan and candied fruit), one bite of its traditional giuggiulena (sesame crunch), and one lick of its latte di mandorla (almond milk) ice cream.

Best (Out-of-Town) Hotel

Salvatore Mancini Nifosi is not your average double-barreled Sicilian nobleman. His architectural training came in handy when he restored a former Knights of Malta fiefdom in the rugged, primordial rural landscape south of Ragusa and turned it into the Eremo della Giubiliana (suites, $555-$890 per night; 39-0932/669-119; www.eremodellagiubiliana.it), the only hotel in southeast Sicily that really makes the international luxury grade. Ask for the Grand Master Suite, a romantic flower-decked tower apartment. In addition to his role as hotelier, Mancini Nifosi is a pilot who keeps up the Malta connection by flying guests to the island for day trips from the hotel's private airstrip ($310 for up to five passengers).

How to Get to Syracuse

Fly to Catania, which is 37 miles north of Syracuse. (There are currently no direct flights from the United States to Catania, but there are plenty of daily connections available from Rome's Fiumicino and Milan's Malpensa airports.) A taxi to Syracuse takes about an hour and will cost approximately $75.

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